7
unorthodox
strategies for
WINNING
Jason Shen
Author’s Note
This book finds it’s origins as a guest blog post I wrote on SebastianMarshall.com, a
wonderful blog with honest, insightful and sometimes provocative stuff about victory
and winning. Here’s what Sebastian said about it:
“I was really honored and thrilled when Jason Shen offered to write a guest post
here at SebastianMarshall.com – he’s an incredibly bright guy with broad
knowledge and skillset, writes well and clearly, and is an all-around good guy. So
I’m really excited to be able to bring you a guest post by him – I imagine you’ll want
to read more by him afterwards, and you can reach him at his website –
www.jasonshen.com.”
The post did very well on his site and was read thousands of times in just a few days.
I’ve decided to expand on it and turn it into a book that you can share with others. I
hope you enjoy it and if you like it, feel free to share it with your friends.
Cheers,
Jason
7 Unorthodox Strategies for Winning. Copyright Jason Shen 2011
Introduction
Recently, I’ve been thinking about ways to win that are less commonly employed – one,
because it’s interesting and two, because I think there is a lot we can learn from
unorthodox methods that work.
That’s what this book is about: strategies that are nontraditional, that are beyond “do
your best and learn from your mistakes” type advice, yet are undeniably ways that help
you win.You might find them strange, but that’s ok because winning isn’t normal.
Some people find the pursuit of winning distasteful or even silly. Others get juiced by the
idea of winning, of kicking ass and taking names, of being the best. I have a feeling that
many of you fall into the second category. This book is for you.
(1) Select an Arena with Weak Competition
If your primary focus is on winning and you don’t care that much about the field of
victory, then take the time to find something where there are few competitors to beat. If
you’re in business, perhaps this is a new venture that focuses on stuff others overlook or
have written off – something advocated in the book Blue Ocean Strategy.
When parents ask me how they can get their kids into a good school like Stanford, I’m
inclined to tell them – quit the piano lessons and soccer practice and have them enroll in
archery or kazoo. Better yet, have them invent their own game/sport/instrument and
instantly become the best in the world at that thing. Elite universities want people who
are the stars/standouts in their field.
Less competition = much greater chance of winning. So look around you – what’s
everyone doing that you might do less of? What is everyone ignoring that you could
dominate?
(2) Conduct Extreme Preparation
There’s doing some advance prep and there’s extreme preparation. The latter – doing
everything in your power to:
■
■
■
■
understand the game/competition/challenge in which you are trying to win
internalize what previous winners have done
analyze your opponent(s) strengths and weaknesses
practice/train what you’re going to do at “show time”
I’ve scored extremely high on my SATs (1580/1600) which puts me in the 99.9 percentile.
Now you may argue that the test isn’t a good indicator of academic ability, (which I would
agree with), but still – I busted my butt to get a good score and did ridiculous amounts of
prep.
The summer before my junior year, I knocked out 10 practice SAT tests. I didn’t just go
fill out the answers – I would go back and check every single answer and every time I
made a mistake, I would make sure never to make that mistake again. I read a separate
book called SAT: 1600 that gave even more advanced tips on how to analyze the test
questions and accurately guess the right answer when you weren’t sure. By the time I got
test day, I was able to finish every section with 10+ mins to spare and went back and
double checked all my answers.
I’ve used this level of preparation to earn 98 and 92 percentile scores on the GMAT and
the MCAT – it’s a lot of work, but that’s what it takes to win.
(3) Winning via Changing the Game
You play someone in a game of chess. You lose. What do you say?
“Come on – let’s do best out of three.”
You’ve just changed the game to increase your chances of winning. Because before, the
assumption was that one game of chess would determine who was the winner. But now,
you have an opportunity to come back and win the “full game”.
If you’re observant, you’ll see that people who are devilish debators will switch up on the
topic on you without you even noticing. All of a sudden you’re defending yourself against
an argument which has nothing to do with your original discussion. They changed the
game under your nose and now you’re losing.
If the rules favor incumbents – figure out how to reframe the situation. Introduce new
variables, make the goals different, leverage some resource that is typically ignored. If you
can change the game to favor your side – you can win.
(4) Simply Refuse to Lose
In a war of attrition, you win by simply being able to take more losses. You just keep
taking hits and keep getting beat down, but you win through sheer force of will. If
someone is fighting you and you just keep getting up every time they knock you down,
they will get tired and therein lies an opportunity to win.
Beth Anne Waters got her GED, then her college degree, then her law degree, then passed
the bar and found biological evidence to exonerate her brother from a crime he didn’t
commit – all while raising two kids. It took her 18 years. They made a movie about it – but
the story is real
Incredible – I mean who does that? Any reasonable person would have given up a long
time ago. But if you simply decide you are not willing to lose and will do whatever it takes
to win, your chances of success go up dramatically.
(5) Join the Winners
If you can’t beat them, join them, the old saying goes. And why not? Felix Dennis wrote a
great book on becoming wealthy and talks at one point about how his publishing company
was faced with a huge competitor who was coming in to the market to wipe him out. He
banded together with another publishing firm of roughly the same size, dug in and battled
it out against the new entrant.
After many years and millions of dollars spent, they finally drove off the big competitor.
But is Felix proud of that moment? Maybe a little, but mainly he curses himself for trying
to fight. He says if he had been smart, he would have switched over to partner with the
competitor and thus easily swept the market and earned lots more money. Perhaps not
the response you expected, but then again his book *was* called How To Get Rich.
There will be times when it’s obvious that your team or your strategy is going to have a
hard time winning. If you’re ok with ditching your team and jumping ship (not something
I necessarily condone) then you might be able to land on the side of victory.
(6) Exploit Weaknesses
The last unorthodox strategy I’ve got for you for winning is to mercilessly exploit
weaknesses. Like any strategy, this advice can be used for good or malevolent purposes –
I hope you choose the former.
My dad really enjoys playing tennis and one thing he tells me a lot is that he wins by
letting the other player make the mistake. He focuses on keeping the ball in play and
trying to throw his opponent off guard whenever he can. I looked up some articles on
tennis strategy and here you have it:
“The first great rule in general tactics: keep the ball in play and give your opponent
another shot at it, rather than risk an error by taking an unnecessary chance.”
Interesting right? I’m all about being aggressive and going after the win, but sometimes,
the best thing to do is to stay cool, play it safe and then work hard to make the other
person lose. And that starts with identifying their not-so-strong parts:
“The first thought that you should have, when you step on to a court for a match, is
“What are my opponent’s weaknesses? Where will he miss most?”
That’s a pretty hardcore approach but a powerful one indeed. In fact, the article seems to
suggest that your opponents greatest weakness (outside of his physical skills) is his
mental focus.
“Nothing is so disconcerting or upsetting to a player as to miss. A magnificent shot,
which beats him completely, doesn’t cause him much mental anguish because, if he
is a sportsman, he will admire it and then not worry about it any more. On the other
hand, each time he sees an important shot of his own sail out of court or into the
net, a player becomes more nervous and less likely to win a match.” (Match Play
Tactics – Exploiting Your Opponent’s Weaknesses)
I love that idea. If you perform well, your opponent won’t get thrown off – it’s the shots he
messes up that really screws with his head. Tennis is a mental game and like all good
mental games, the key is to get inside your competitors’ heads and break them down.
(7) Get the Timing Right
This strategy comes from reader - chegra - who offered some wisdom he learned from Six
Secret Teachings, a Chinese treatise on civil and military strategy written in the eleventh
century BC. In his words:
“Use timing to win. Certain times of the day or month or year goals are easily
accomplished and obstacles easier to overcome, use those times to your
advantage. For instance on Hacker News, certain times of the week it is easier to
get a post on front page.”
If you want to climb Mount Everest, you’ll want to wait until the storms die down. If you
want to kiss a girl, you’ll want to wait until the conversation has died down and she’s
looking coyly at you. If you want to ask for a raise, you should do it right after you’ve
nailed a big project.
Think and observe how others get things done and you’ll find that timing likely plays a
role. Get the timing right and many more things will go your way.
So there you have it – some uncommon and unorthodox strategies for winning. I hope
you get some value and some victory out of them.
Thanks for reading.
About the Author
Jason Shen is obsessed with kicking ass and making things happen. He
does sales & marketing at a tech startup in the SF Bay Area, cohosts the
Rejection Therapy Podcast and captained the Stanford gymnastics NCAA
championship-winning team. Find him at JasonShen.com